Best Halloween Ever
by Hypnotoad76
Summary: Annie dresses up as a sexy video game character for Halloween, and drives Jeff wild.
1. Chapter 1

"Oh, that's nice. I'm not the only one who decided to wear an animal costume," Shirley cooed as she walked into the study room and saw Britta adjusting the headband holding her floppy dog ears.

"Hey Shirley," Britta said uncertainly as she took in the woman's costume. "Your…a cat, right?"

"Not just any cat. A cute famous grey cat that's in a famous comic strip."

"Right…which is…" she stated, drawing out the last word to buy some time. Luckily for her Abed and Troy walked in at that moment, giving her an out. "Wow, you two look great."

"Thanks pretty dog lady," Troy said in a thick Italian accent. Both men had on blue overalls and white gloves, along with thick fake mustaches. Troy wore a red long sleeve shirt and red hat and padding to make himself look heavier, while Abed sported a green shirt and hat.

"Did Annie come with you?" Shirley asked.

"She said she'd meet us here," Abed said. "She had to make a few adjustments to her costume."

"What's she coming as?" Britta asked.

"She wouldn't tell us. We wanted her to be Princess Peach so we'd match, but she said she already had something picked out," Troy stated with disappointment.

"She did say she was also coming as a video game character," Abed exclaimed.

"Okay everyone. Famous alumni approaching."

The four of them turned around as Pierce walked into the room. "Pierce...you look comfortable," Troy said. The older man was wearing black silk pajamas and slippers, and a red smoking jacket.

"I'm more then comfortable. I'm Hugh Hefner. The ultimate ladies' man."

"Ugg," Britta complained. "You're emulating someone who's objectified women by forcing them to value themselves only for taking off their clothes-." She stopped her rant as everyone groaned loudly. "Fine, but someday you'll wise up and realize I'm right."

"Britta, its Halloween. Can't we just enjoy ourselves," Shirley asked.

"I agree," Pierce stated. "I should be able to emulate an American hero, just like Shirley has every right to be a grey squirrel."

"I'm Nermal, from Garfield," Shirley angrily stated (while Britta, Troy and Abed simultaneously said "OH")

"Okay, let's start this thing; I have another party to get to in exactly one hour and nineteen minutes," Jeff said as he strolled in.

"Wow, I didn't think you'd show up Winger," Britta said. "And what's your costume? Or lack of one," she stated at his normal attire.

"I'm a graduate visiting Greendale. That's my costume. What are you? A long eared wolf?"

"Basset hound."

"Of course. Where's Annie?"

"Hey guys," Annie stated at that exact moment as she walked into the room. She stopped when everyone stared at her in complete surprise. "What?"

Annie was wearing a tight sleeveless blue shirt, a pair of tiny dark brown shorts, and hiking boots. She had a gun holster strapped to each thigh, with a gun in each one. Her hair was pulled back into a ponytail to complete the outfit.

"Wow, you look great Annie," Troy said.

"Nice," Abed simply said. "You went with the classic Lara Croft look instead of the later game versions."

"Thanks," she said. "I was going to braid my hair but I didn't have time."

"You still look just like her."

"Yes, that's a…nice outfit." Shirley said with the slight tone of a disapproving mother.

"It's Halloween," Annie exclaimed, catching Shirley's tone. "You should be able to dress up and have a bit of fun. Right?"

"Right," Britta said, actually coming to Annie's defense. "And at least you came as an actual character instead of a generic slutty person. I mean, Quendra's a sexy hockey player. How does that even work?"

"You crop a jersey into a midriff top and then-."

"Okay Abed, Yes, it's possible. But the point is-."

"Can we just go to the cafeteria already?" Pierce asked. "Before we're here all night."

"It's barely seven," Troy stated.

"Plus, you're in pajamas," Britta said as they all started walking. "You can go to the lounge and take a nap if you need to."

Normally this would have been Jeff's cue to make a joke at Pierce's expense. But right now he couldn't care less about making fun of anyone. All he could focus on was Annie, and how freaking hot she looked in that outfit. If anything, her shorts were even smaller than the ones she wore with her infamous paintball outfit. And while the top didn't allow for much showing of cleavage, it still highlighted just how impressive her…feminine charms were.

_Don't get any ideas, he thought. This isn't some random girl. It's Annie. Just Annie dressed as a video game character. An insanely hot video game character. _His eyes widened as he watched her squat down to re-tie the laces on one of her boots. _This is going to be a long night. _

XXXXXXXXXXXX

"Hope you're enjoying the 'Hallowscream' party. Don't forget, there's bobbing for grape eyeballsand blood punch to enjoy," Dean Pelton stated as he made his way through the crowd. He smiled heavily as he made his way over to Jeff. "Jeffrey, so good to see one of our most famous graduates gracing us."

"Dean," Jeff said, taking in the go-go dancer outfit the administrator was wearing. 

"Jeffrey, you're no longer a student here. Call me Craig."

"Dean Pelton." They both looked over as a security guard came rushing over. "You need to come quick. We caught more students trying to change the playlist on your I-pod."

"Oh for crying out-this is the fifth time someone's tried to stop the music. What does everyone have against Miley Cyrus?"

"And I thought the year he only played Backstreet Boys was bad," Jeff muttered as the dean walked away. He shook his head before looking through the crowd until he spotted Annie by the refreshment table, pealing the foil off a cupcake. He knew it made him seem like a creepy stalker, but he couldn't keep staring at her. His eyes took in how great her chest looked in that top before traveling down, admiring just how much of her legs were on display, before moving upward and appreciating just how good those shorts made her butt look.

He looked away as she caught his eye, smiling as she walked over to him. "Hey Jeff."

"Lara."

She giggled as his joke before frowning slightly. "How come you didn't dress up?"

"I don't know. I wasn't even sure I was going to come. And don't give me that look," Jeff exclaimed as she gave him the typical 'Annie look'.

"I wasn't giving you a look."

"Yeah, you were," he said in a somewhat playful tone. "You're got frosting on your face." He gently caressed the side of her mouth with his index finger, wiping the orange frosting off her. Annie closed her eyes, sighing a bit in pleasure. Before she could stop herself, Annie moved her mouth over Jeff's finger and sucked it clean. He looked at her as she opened her eyes, both of them surprised at the boldness of her action.

"Va, vhat have ve have here," Sean Garrity said as he swooped towards them, speaking in a bad Dracula accent to go with his costume. "Tvo people to vake members ov my army ov the night."

"I'd be careful there," Jeff stated. "She's a skilled adventurer who's a crack shot."

"Yes, while we're on that," Professor Garrity continued in his normal voice. "I have to remind you to put those prop guns back in the prop closet when you're done with them. I'm directing an alternate take on Death of a Salesman and I need them for the Mexican standoff scene. Have a good night." With that he whipped his cape over his face before hurrying off.

"That sounds like the worst play I have to go see," Jeff said. He looked back at Annie, feeling the same attraction he'd previously felt rise to the surface. He almost unconsciously felt himself moving in to kiss her when Troy and Abed chose that moment to race past them.

"Abed quick, I think Annie's Boobs ran that way!"

"I'm on it!"

"Wait for me!" Brita yelled as she hurried after the two men.

Jeff shook his head at yet another distraction. "Seems like the universe is telling us-."

"Come on," Annie said sternly as she took Jeff's hand and pulled him out of the cafeteria. She was sick of the two of them having a moment, only for someone to come by and ruin anything from happening. It was time she took control instead of just waiting and hoping.

Jeff allowed Annie to lead him down the hallway until they reached the supply closet the group used to sometimes gather in. "Annie, what are we-?" His words failed him as she shoved him into the room and kissed him hard. He grabbed hold of her as he kissed her right back, running his hands down her back. A part of him screamed that they should stop. But an even greater part told him to shut up and allow this to happen.

Annie pulled back from Jeff just long enough to make sure the door was locked before they resumed their kissing. Their tongues danced together as she unhooked the straps of her holsters, a clang heard as they dropped to the ground. She moved her hands under Jeff's shirt, running her fingers over his stomach and chest. Jeff quickly pulled his shirt off, momentarily tangling both their heads together. They laughed before he was able to free them.

Annie took a step back, admiring Jeff in just a pair of pants. It was a sight that while not new, still remained one she loved seeing. She took a breath before pulling her own shirt off, standing a bit nervously in just a bra. Her nervously evaporated as Jeff pulled the cups aside, freeing her boobs. He took a moment to admire them before leaning down, pressing his body against hers as he took one of those fantastic breasts in his mouth, biting her nipple hard enough so it was pleasurable with just the right amount of pain. He kissed and sucked one breast and squeezed the other before alternating his mouth to the other. He felt Annie run a hand over his erection and moaned as it grew even stiffer. Soft mewling sounds escaped Annie as she moaned in pleasure over the attention Jeff was lavishing over her body.

"Get on your back and take your pants off," she told him. Jeff readily obeyed, laying down and pulling his jeans and boxer briefs off as quickly as he could. Annie unbuckled her belt and wiggled out of her shorts and panties. She straddled Jeff's waist, naked except for her hiking boots, and guided him into her.

"Holy, Annie!" Jeff moaned as she slowly lowered herself until he was completely inside of her. She braced her hands on his legs as she pushed herself up a few inches before lowering herself back down. She moved slowly at first, but began to pick up speed as her body became accustomed to having Jeff inside of her.

Jeff watched Annie fuck herself on his cock for several moments, simply enjoying the experience of being surrounded by her warm, wet walls. Wanting this to feel as good for her as it did for him, Jeff leaned up into a sitting position and rubbed his thump against her clit. Annie gasped and shuttered at this new sensation, arching her back as Jeff put his hand on the base of her spine to anchor her. He moved his own hips as he began to piston himself in and out of her while continuing to stroke her clit. They both moved in and out of one another as their lips once again met and they Frenched like rabid lovers.

Jeff desperately recited baseball statistics in his head as he fought off his approaching orgasm, determined to hold out until Annie had also arrived. He quickened his thrusting and moved his thump more vigorously over her clit. Finally he felt her warm walls grow even hotter as she came, moaning his name as she shuttered in pleasure. He arrived a moment later, crying out as he experienced the most intense orgasm of his life.

Almost in a daze, Jeff leaned down, holding onto Annie until they were laying together on their sides. He kept his arms wrapped around her as they lay there in the closet, utterly amazed at what had just transpired between them.


	2. Chapter 2

It felt like an eternity until Annie was able to form a coherent thought. But once she regained her higher brain functions the realization of what had just happened hit her. She and Jeff had finally slept together. Not only that, but it had been her idea. A part of her was surprised it happened so quickly. Although truth be told, the last few years had been nothing but build up. It was about time a move had been made.

But as she thought about it a frown settled on her face. If it had been with another guy she'd be grinning ear to ear, wondering how things were going to go. But this was Jeff, and she had no illusions of where this would lead to. Jeff would now become awkward and want to avoid her. Hopefully they'd eventually be able to remain friends, like he did with Britta. But she was smart enough to know that her childish fantasies involving Jeff in any kind of dating or boyfriend scenario were just that: childish fantasies.

Jeff looked at her as she pulled away and started getting dressed. "You okay?" he asked as he started putting his own clothes on.

"I'm alright."

Jeff paused in buttoning his pants as he caught the tone in her voice. "What's wrong?"

"Nothing Jeff. I know how this goes."

"What are you talking about?" he asked.

"I mean I know how things are after you sleep with a woman. You move on." Annie glanced over, a bit surprised at the look he was giving her. "Don't act surprised, it's not exactly a hidden secret. I just want you to know that I'm not going to act like this is something it's not and think we're suddenly going to start dating. I'm not going to become 'crazy love sick Annie' just because we had sex. This was just like you're other hook ups."

Jeff looked at her as she finished getting dressed and strapped her gun holsters back on. Logically he should be relieved at her assumption that this was simple no strings attached sex. And if it was any other woman he would have breathed a huge sigh of relief. But this was Annie. And while it could be annoying and naive at times, deep down he liked that she expected more from a guy then just a meaningless hook up. It proved just how different and special she actually was. He didn't want her to act like everyone else. And even more importantly, he realized that he didn't want to treat her like everyone else.

"Come on," he told her as he pulled them to their feet and lead her out of the closet.

"Jeff wait, where are we going?

XXXXXXXXXXXX

"And if you'll look to your left, you'll see Pampkin's ale house. Legend has it that Ma Barklet, wife of the original owner, was killed in 1949 when a barrel of ale fell over and crushed her to death. And they say on some nights people can actually see her ghost sitting on an empty bar stool, waiting for her husband to find her." The tour guild waited until most of the group took pictures of the building before loudly clearing his throat. "Okay everyone. Let's continue on with the 'walking tour of Greendale ghost sightings'."

Jeff desperately tried not to sigh as the tour group started walking to their next destination. It was partially his own fault they were here right now. Once they got outside Jeff spotted a group of people across the street from the school about to embark on a tour of Greendale haunted hotspots. Immediately he suggested doing that, which was why they had now spent the past forty minutes walking to one inane location after another.

But even though he thought this was stupid as anything, he knew he had to do this. After what Annie said after they'd slept together, he had to prove to her (and maybe also to himself) that he didn't think of her as a woman he was just going to toss aside now that they'd had sex. Which was why he'd pretty much looked for the first thing they could do that qualified as a date.

Though he wished he'd picked something that wasn't so moronic.

As they walked Jeff looked over at Annie, seeing her shiver a bit. She'd left her jacket in her car and her outfit wasn't exactly convenient for a nightly fall stroll. He'd lend her his coat at the start of the tour (and bit his tongue every time she bent her elbows), but could tell she was still cold. "You okay?"

"I'm fine."

"If you want we can go home."

"No, I'm good." True, she thought the tour was kind of stupid. But in a silly amusing way. And she had a feeling this was important for some reason to Jeff.

Besides, having Jeff volunteer to do something like this was a rarity in and of itself. And she wasn't about to spoil it.

XXXXXXXXXXXX

"And now we come to the final, and some say, scariest stop on the tour. Get ready to tighten your sphincter's, as we approach, a grave yard."

"You've got to be kidding me," Jeff muttered as people actually took out cameras and started taking pictures.

"Obviously, here is the final resting place for many residents of Greendale. And it's possible that on a night just like this, some poor lonely soul might be wandering the earth trying to finish something that plagued them in life. That concludes our tour. If you'd like to make donations, it would be greatly appreciated. Have a good, and spooky, night."

"That may have been the worst thing I've ever suffered from." Jeff finally said as people actually gave the inane tour guide money. "Seriously," he groaned as Annie gave the guide a dollar.

"What?"

"You actually gave that guy money."

"He was entertaining."

"You thought that tour was good?" he asked.

"Okay, yes, it was lame. But I still enjoyed it."

"Well I'm glad one of us did."

"If you hated it so much why did you insist we go?" she asked Jeff, folding her arms across her chest.

"I wanted…I wanted to do something that was a date, okay."

Annie's face softened as she uncrossed her arms, a soft smile creeping up her face. "So this was supposed to be a date?"

"What else would you call taking someone on the worst ghost hunt ever?"

Annie chuckled at that, before the smile left her face. "Wait. Did you just do this to try and prove what happened in the closet wasn't just a one night stand?"

"No…not exactly." He sighed, wishing she wasn't smart enough to see through his fly by the seat of his pants plan. "This is pretty new territory for me. I generally just date woman so I can sleep with them. So going out with someone after we've had sex…hopefully you're bright enough to see that it means something."

He figured he said something right, since Annie wrapped her arms around him and kissed him. She then pulled back, taking hold of his hand. "Come on."

"Where are we going?"

"We're going to try to find a ghost," she said playfully. "I mean, we are in a possibly haunted graveyard."

"Seriously? I had enough of ghosts on the tour."

She giggled when suddenly she heard a snapping sound, like twigs breaking. "What's that?"

"What's what?"

"I just heard something."

"Annie, come on. This ghost thing is getting old."

"Jeff I swear I heard something." She grabbed his arm as the sound of crunching leaves was heard. "There. Over there."

Jeff looked ahead, starting to grow concerned. "Stay behind me." He slowly walked forward, making sure Annie was blocked by whatever might come at them. "Hello?"

Suddenly they both yelled as a caped figure lunged out at them. The figure fell back at a gun was fired at him. Jeff looked at Annie, seeing her holding one of the prop guns from her holster. "What the hell? You shot him?"

"I panicked, okay!"

"OW!" They both whipped around as they saw that the caped man was Professor Garrity. "I think I hurt my ankle there."

"Professor Garrity?" Annie asked. "What are you doing here?"

"I came to get my prop guns. I told you to return them and instead you took them out of the school."

"So you decided to stalk us," Jeff angrily asked.

"I was trying to make a dramatic point. And that is that prop guns should not be taken out of the school. Now…" He held out his hand, beckoning for his theatrical property back.

"Here, you can have them back," Annie said as she took them from her holsters and handed them to the Professor.

"Thank you. Though next time I'd appreciate it if you didn't fire them at me, even if it is just a prop. Haven't either of you ever seen The Crow?" He started walking away when he turned back at them. "Though I will say, if you decide to invite me to your wedding I'll have one hell of a story to say in my toast."

The two of them looked at each other as Professor Garrity walked away, shocked at what they had just heard. "So, he's crazy," Annie quickly said.

"Bat shit nuts. Did he think he was an actual vampire, jumping out at us like that?"

They both laughed nervously, trying to work through the awkwardness Sean's words had left. But as Jeff looked at Annie in the moonlight he thought about it, and realized he wasn't feeling the complete disgust he usually felt when the thought of marriage entered his mind.

"Well, I should probably get home," Annie said, pulling Jeff out of his thoughts.

"Okay," Jeff said uncertainly. "I mean, if you really want to. But it's still kind of early. We can do something else."

"Like what?" she asked, her eyes shining brightly.

Jeff slowly smiled as an idea came to him. It was a bit mean considering how she felt about scary movies. But it could also have some advantages. "How about we go to the movie theater on Willis Street. They always show classic horror movies on Halloween."

"Um, sure," she said uncertainly.

XXXXXXXXXXXX

"Why did I talk you into letting me watch _A Nightmare on Elm Street_?" Annie asked as they exited the theater. "I'm going to have nightmares tonight."

"Careful. Then Freddy Kruger will come and get you," Jeff said as he ran his fingers up her arm.

"Stop that!" Annie yelled, swatting his hand away. "You're mean."

"Come here." Jeff put an arm around her, feeling some of her annoyance slip away. "I don't know how you can hate horror movies. What about that werewolf story you told everyone on Halloween a few years ago?"

"That was a story. I'm fine with scary stories and books…most of them. But I just don't like horror movies. There's a reason I never saw any Freddy movie before."

"Well to be fair, you didn't actually see the whole movie tonight either," he whispered in her ear.

Annie blushed at that one. During each scary moment Annie ended up grabbing onto Jeff whenever she was frightened. And eventually this lead to them making out for the whole second half of the movie. As it was she had no idea how Freddy ended up being defeated.

"Wait?" she asked as she looked up at Jeff. "Did you suggest seeing a scary movie so I would get frightened and we'd make out?"

"And I thought you were the clever one." He grinned as she playfully slapped him on the chest. "Completely worth it."

XXXXXXXXXXXX

"It's not a kid's book Jeff, its young adult."

"That's still a kid's book."

Annie groaned, taking a sip of her coffee to stall their argument. After the movie they walked around town for a while. Annie was a bit hungry, so they ended up stopping at a diner to get something to snack on.

"I still think you'd enjoy it."

"Annie, I'm not reading _Perks of Being a Wallflower_. Isn't it a girly book anyway?"

"No. It's about a lonely high school freshman boy who meets some friends who make his life better. I read it in high school and loved it. Though I think I can relate to it better after going to Greendale. But trust me, it's really good. And it's definitely not a kid's book. There's sex and drug use and other adult situations," she finished playfully.

Jeff laughed as Annie wiggled her eyebrows suggestively. "You're cute when you're silly."

"Thanks." She reached for the last mozzarella stick, before pulling her hand back. "Did you want it?"

"It's all yours." Jeff watched as Annie popped the stick in her mouth, trying not to think too many dirty thoughts as she swallowed and licked her lips. "So…what are you reading now?"

"I reread _Catching Fire_ last week since the movie is coming out soon. And I just started reading _The Ocean at the End of the Lane_. What about you, are you reading anything?"

"Not at the moment. Though I keep meaning to read _Threat Vector." _

"You like Tom Clancy?" Annie asked.

"I've read a number of the Jack Ryan books. So I'd wouldn't mind reading another one."

"I've never read any of them. Would I like it?"

"They're good if you like espionage and stuff like that. I'd say try one and see if you like it."

"How about…I'll read a Jack Ryan book if you read _Perks of Being a Wallflower_," Annie countered with a grin.

Despite how annoying her grin was, Jeff wouldn't help smiling along with her. "Fine. You've got a deal."

XXXXXXXXXXXX

"I should really get inside," Annie moaned as Jeff pulled her into yet another kiss. They'd been standing in front of her build for the past ten minutes. But every time Annie tried to go inside, Jeff kept giving her another reason to not go up yet.

"Just a few more minutes." He said, his voice muffled from his lips being pressed against hers.

"What if Troy or Abed comes out here?"

"I don't care."

At that Annie pulled away, looking at Jeff suspiciously. "You don't care if one of them finds out about tonight? And they tell the rest of the group."

"Annie, I technically just went on three dates with you and actually had a good time. Plus, there was the pretty amazing sex we had in the closet." He chuckled at the blush spreading across her face before continuing. "I don't know where this is going, but I'd like to see where it leads to."

"So, you actually want to try it?" Annie asked. "You want to date and tell the group we're together?"

Annie watched as Jeff took his phone out and pulled her into him, heading the click of his camera as he kissed her. He worked the screen for a few moments before he showed her his phone. "That answer your question?"

Annie looked at his phone, seeing that he'd just sent the picture to the group with the caption 'we're dating as of now. ttyl'. She smiled as she pulled Jeff into another kiss, both of them ignoring their phones buzzing with incoming texts.


End file.
